Scott Disick Dating History: Kourtney Kardashian, Sofia Richie and More

When it comes to A-listers with complicated love lives, Scott Disick definitely comes to mind. He’s had long-term relationships with ex-girlfriend Sofia Richie, as well as ex Kourtney Kardashian, but the former Keeping Up With the Kardashians star has also had a handful of other romantic relationships in between, including his most recent relationship with ex-girlfriend Amelia Gray Hamlin.

Scott’s dating history also includes actress Bella Thorne, celebrity stylist Chloe Bartoli and model Bella Banos. Prior to settling down with Amelia in late 2020, the Talentless founder and Sofia had whirlwind romance.

On May 21, 2020, a source confirmed to Life & Style that Sofia and Scott decided to “take some time apart” following his brief stint in a Colorado rehab facility. Days later, on May 27, the couple called it quits for good after nearly three years together … well, sort of.

“Scott and Sofia are giving love another shot. They’re keeping it on the down-low and are still figuring things out before making it official,” a separate source exclusively told Life & Style less than two months after their breakup.

“Scott is working on himself so they don’t want to jump into a full-blown relationship or anything like that,” the insider added. “They’re taking baby steps, and are spending time together and seeing where it goes.”

Scott and Sofia first sparked reconciliation rumors after being spotted together on the 4th of July. “They missed being around each other,” the source explained. “It’s one of those ‘absence makes the heart grow fonder’ situations.” The two broke up again in mid-August.

In between all the Sofia drama, it briefly appeared as though the Flip It Like Disick producer and Kourtney were giving their relationship another chance. The former flames, who share three children — Mason, Penelope and Reign — spent a lot of time together and even shared a few flirty exchanges on Instagram.

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However, things seemingly stayed platonic between them. “There’s a lot of water under the bridge, and while Kourtney loves having Scott around the kids more, she’s not about dating him again,” In Touch previously reported. “That’s not something she’s ready to embrace.”

Kourtney is now engaged to Blink-182 drummer Travis Barker. An insider told Life & Style the Poosh founder’s hot romance with the musician has caused tension with Scott, and the coparents have been “secretly clashing for a while” behind closed doors.

To see a complete breakdown of Scott Disick’s dating history, scroll through the gallery below.

Chloe Bartoli

Similarly to a lot of Scott’s relationships, he and Chloe were very on-again, off-again. They apparently began hooking up in 2010 when Scott and Kourtney were on a break. “He was hot and heavy with Chloe for a brief time,” a source told Us Weekly in 2015. That year, they reunited once more. Scott and Chloe were last linked in May 2017, just months before he settled down with Sofia.

Bella Banos

In October 2020, Scott and the 24-year-old model were spotted dining at Nobu Malibu. However, their relationship dates all the way back to 2017. Bella and Scott were first linked after taking a trip to Costa Rica together that year. “At first, Scott was just my friend, but he got to know me on a different level,” the brunette beauty told In Touch at the time. “We’re super connected.”

In December 2021, Scott and Bella reignited romance rumors after vacationing together in St. Barts.

Amelia Gray Hamlin

Scott and Amelia raised some eyebrows after arriving to a 2020 Halloween party at the same time. However, it’s common knowledge the E! personality and Lisa Rinna‘s daughter run in the same social circle.

However, they hit a rough patch and split the following September after Younes Bendjima leaked an alleged DM from the reality TV dad shading Kourtney’s PDA-packed trip to Italy with her boyfriend, Travis.

Rebecca Donaldson

Straying away from American women! A day after Kourtney and Travis had an impromptu wedding ceremony in Vegas in April 2022, Scott was seen with a new leading lady.

Rebecca and the Flip It Like Disick star spent a day out in Malibu on April 5. They were later seen in the early morning of April 6, holding hands while leaving a party at On The Rox in Los Angeles. While they attended The Kardashians, Scott was later seen out with Bachelor alum Corinne Olympios in Miami, causing speculation that they had split.

Holly Scarfone

Scott and the Too Hot To Handle season 3 star were first spotted out at the Talentless founder’s go-to restaurant, Nobu Malibu, on February 24, 2022.

The pair went on a Paris vacation the following month where the two sent cheeky Instagram comments to one another. Holly posted a picture of herself wearing a black lingerie set with the Eiffel Tower in the background.
“Where is my photo credit,” Scott’s comment read on the March 7 Instagram post. The reality star then re-captioned her photo, “Lounging in the city of amour. Photo creds @letthelordbewithyou.”

After Scott moved on with Rebecca, Scott seemingly inspired reconciliation rumors with Holly by leaving a very flirty comment on her Instagram in May 2022. It all started when Holly posted photos of her in a bodysuit, writing in the caption, “Oh lord she’s @talentless.” Responding tot he tag, Scott replied, “I can think of a few talents you have right off the top of my head, no pun intended.”